Studies on the structure and biosynthesis of tridentoquinone and related meroterpenoids from the mushroom Suillus tridentinus (Boletales)

European Journal of Organic Chemistry

Volumn , Issue 5, 2008, Pages 816-825

  Lang, Martin ^a   Mühlbauer, Andrea ^a   Gräf, Claudia ^a   Beyer, Jürgen ^a   Lang Fugmann, Susanne ^b   Polborn, Kurt ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Biosynthesis; Isotopic labeling; Meroterpenoids; Mushrooms; Natural products

Indexed keywords

EID: 53649089889     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700908     Document Type: Article

References (45)

1. H. Besl, H.-J. Hecht, P. Luger, V. Pasupathy, W. Steglich, Chem. Ber. 1975, 108, 3675-3691.
2. P. C. Beaumont, R. L. Edwards, J. Chem. Soc. C 1969, 2398-2403.
3. a) C. Tringali, M. Piattelli, C. Geraci, G. Nicolosi, J. Nat. Prod. 1989, 52, 941-947;
4. b) T. Hayashi, A. Kanetoshi, M. Ikura, H. Shirahama, Chem. Pharm. Bull. 1989, 37, 1424-1425;
5. c) H. Besl, A. Bresinsky, Pl. Syst. Evol. 1997, 206, 223-242.
6. H. Schwarz, V. Pasupathy, W. Steglich, Org. Mass Spectrom. 1976, 11, 472-478.
7. a) A. Bax, R. Freeman, S. P. Kempsell, J. Am. Chem. Soc. 1980, 102, 4849-4851;
8. b) A. Bax, R. Freeman, T. A. Frenkiel, J. Am. Chem. Soc. 1981, 103, 2102-2104;
9. c) Review: J. Buddrus, H. Bauer, Angew. Chem. 1987, 99, 642-659;
10. Angew. Chem. Int. Ed. Engl. 1987, 26, 625-642.
11. A. Mühlbauer, J. Beyer, W. Steglich, Tetrahedron Lett. 1998, 39, 5167-5170.
12. M. Gill, W. Steglich, Prog. Chem. Org. Nat. Prod. 1987, 51, 1-317.
13. W. Steglich, Pure Appl. Chem. 1981, 53, 1233-1240.
14. M. Lang, S. Lang-Fugmann, W. Steglich, Org. Synth. 2002, 78, 113-122.
15. J. Beyer, S. Lang-Fugmann, A. Mühlbauer, W. Steglich, Synthesis 1998, 1047-1051.
16. 3- or CAN-mediated reaction of enolizable 1,3-diketones with olefins, see K. Kobayashi, H. Umakoshi, K. Hayashi, O. Morikawa, H. Konishi, Chem. Lett. 2004, 33, 1588-1589 and references cited therein;
17. b) For the use of benzene-1,2,4-triol instead of the unstable 2-hydroxy-1,4-benzoquinone, see: K. Kobayashi, T. Uneda, K. Tanaka, M. Mori, H. Tanaka, O. Morikawa, H. Konishi, Bull. Chem. Soc. Jpn. 1998, 71, 1691-1697.
18. 13C](geranylgeranyl)benzene or of meroterpenoid 14* (cf. Table 1) had been administered to the fruit bodies (no incorporation into 11).
19. All our attempts to convert tridentoquinone (1) into deoxy compound 11 were unsuccessful.
20. The belamcandones, red dioxotetrahydrodibenzofurans from the seeds of Belamcanda chinensis and Iris pallasii (Iridaceae), may be formed by an analogous mechanism: a) K. Seki, K. Haga, R. Kaneko, Phytochemistry 1995, 38, 703-709;
21. b) K. Seki, K. Haga, R. Kaneko, Phytochemistry 1995, 38, 965-973.
22. The possibility that tridentorubin (5) is at least partially an artefact, can not be excluded. It could be formed non-enzymatically from hydroxybenzoquinone 10 and tridentoquinone (1) in the fruit bodies or during the work-up procedure, including the polyamide chromatography. The latter is known to catalyze the dimerization of hydroxybenzoquinones (E. Jägers, W. Steglich, Angew. Chem. 1981, 93, 1105;
23. Angew. Chem. Int. Ed. Engl. 1981, 20, 1016-1017). Hydroxyquinone 10 could be formed from the bolegrevilol (3) present by hydrolysis and subsequent oxidation of the resulting triol 8. The greatly varying yields of 5 in the individual isolations point to this possibility.
24. R. von Ardenne, W. Steglich, Z. Naturforsch., Teil C 1974, 29, 446.
25. A. Mühlbauer, Dissertation, Ludwig-Maximilians-Universität, München, 1998.
26. M. Lang, W. Steglich, Synthesis 2005, 1019-1027.
27. C. Graebe, Justus Liebigs Ann. Chem. 1866, 139, 134-150.
28. J. Thiele, Ber. Dtsch. Chem. Ges. 1898, 31, 1247-1249.
29. R. L. Shriner, P. McCutchan, J. Am. Chem. Soc. 1929, 51, 2193-2195.
30. G. W. Kabalka, N. K. Reddy, C. Narayana, Tetrahedron Lett. 1992, 33, 865-866.
31. M. V. Bhatt, S. U. Kulkarni, Synthesis 1983, 249-282.
32. J. S. Amato, S. Karady, M. Sletzinger, L. M. Weinstock, Synthesis 1979, 970-971.
33. a) M. Tamura, J. Kochi, Synthesis 1971, 303-305;
34. b) M. Bogenstätter, A. Limberg, L. E. Overman, A. L. Tomasi, J. Am. Chem. Soc. 1999, 121, 12206-12207.
35. F. M. Hauser, S. R. Ellenberger, Synthesis 1987, 723-724.
36. C. C. Kanakam, N. S. Mani, G. S. R. Subba Rao, J. Chem. Soc. Perkin Trans. 1 1990, 2233-2237.
37. Elemental analysis of the unlabeled compound.
38. a) J. Pitha, J. Milecki, H. Fales, L. Pannell, K. Uekama, Int. J. Pharm. 1986, 29, 73-82;
39. b) J. Pitha, US 4727064, 1988; Chem. Abstr. 1989, 110, P 179558 c.
40. a) R. R. C. New (Ed.), Liposomes: a Practical Approach, IRL Press, Oxford, New York, Tokyo, 1990;
41. b) D. D. Lasic, Liposomes: from Physics to Applications, Elsevier, Amsterdam, London, New York, Tokyo, 1993.
42. We thank Dr. Helmut Besl, University of Regensburg, Germany, for providing S. tridentinus mycelium cultures (stem no. 468).
43. G. M. Sheldrick, SHELXS-86, Program for the Solution of Crystal Structures, University of Göttingen, 1990.
44. G. M. Sheldrick, SHELXTL-Plus, REL. 4.1, Siemens Analytical X-RAY Instruments Inc., Madison, WI, 1990.
45. L. Zsolnai, G. Huttner, ZORTEP, University of Heidelberg, Germany, 1994.